| 1. Round | 19/08/2000 | Chelsea FC | - | West Ham United | 4:2 |  |
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| 2. Round | 22/08/2000 | Bradford City | - | Chelsea FC | 2:0 | ||||
| 3. Round | 27/08/2000 | Aston Villa | - | Chelsea FC | 1:1 | ||||
| 4. Round | 06/09/2000 | Chelsea FC | - | Arsenal FC | 2:2 | |
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| 5. Round | 09/09/2000 | Newcastle United | - | Chelsea FC | 0:0 | |
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| 6. Round | 17/09/2000 | Chelsea FC | - | Leicester City | 0:2 | ||||
| 7. Round | 23/09/2000 | Manchester United | - | Chelsea FC | 3:3 | |
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| 12. Round | 04/11/2000 | Southampton FC | - | Chelsea FC | 3:2 |
Italy
